N-(3-Aminopropyl)-N-dodecylpropane-1,3-diamine

• CAS: 2372-82-9
• Catalog Number: ACM2372829
• Category: Main Products
• Molecular Weight: 299.53824
• Molecular Formula: C₁₈H₄₁N₃
• Synonyms: N-(3-aminopropyl)-N-dodecylpropane-1,3-diamine;LAURYLAMINE DIPROPYLENEDIAMINE;Bis(aminopropyl)laurylamine;1,3-Propanediamine, N-(3-aminopropyl)-N-dodecyl-;LONZABAC12.100;N-3-AMINOPROPYL-N-DODECYL-1,3-PROPANEDIAMINE;N-(3-Aminopropyl)-N-dodecylpropan-1,3-diamin;3-Propanediamine, N-(3-aminopropyl)-N-dodecyl-1
• IUPAC Name: N'-(3-aminopropyl)-N'-dodecylpropane-1,3-diamine
• Canonical SMILES: CCCCCCCCCCCCN(CCCN)CCCN
• InChI Key: NYNKJVPRTLBJNQ-UHFFFAOYSA-N
• Boiling Point: 386.1ºC at 760mmHg
• Flash Point: 184.5ºC
• Density: 0.880
• Appearance: colorless or light yellow transparent liquid
• EC Number: 219-145-8
• Exact Mass: 299.33000
• Packing Group: III

Case Study

Toxicological evaluation of N-(3-Aminopropyl)-N-dodecylpropane-1,3-diamine

Hartwig, A., Michael Arand, and MAK Commission. The MAK Collection for Occupational Health and Safety 8.1 (2023): Doc011.

N'-(3-Aminopropyl)-N'-dodecylpropane-1,3-diamine [2372-82-9] was evaluated and maximum concentrations (MAK values) were derived for workplaces, considering all toxicological endpoints. The key effects were cardiomyocyte degeneration and lymphohistiocytic infiltration in skeletal muscle of male rats. No NOAELs could be derived for these effects. The LOAEL was 4 mg/kg bw. Extrapolating the NAEL to 1.3 mg/kg bw yielded a MAK value of 0.05 mg/m3 for the inhalable fraction. The derivation of the MAK value is conservative, as the determined oral absorption is very low and for inhalation absorption, a default value of 100% was assumed due to the lack of experimental data. N'-(3-aminopropyl)-N'-dodecylpropane-1,3-diamine is basic and therefore corrosive to rabbit skin, so an irritation potential to the respiratory tract must be assumed. No inhalation studies are available. Compared to several primary, secondary and tertiary amines with MAK values between 1 and 13 mg/m, N'-(3-aminopropyl)-N'-dodecylpropane-1,3-diamine has almost the same or lower basicity. Therefore, a MAK value of 0.05 mg/m should prevent local irritation effects. Since the critical effects are systemic, the substance is classified in Peak Limit Category II. Since the half-life in the blood is at least 28.5 hours, an offset factor of 8 is set. The NOAELs for developmental toxicity in rats and rabbits are 22.5 and 9 mg/kg bw and day, respectively, which can be scaled to concentrations of 1 and 0.66 mg/m2 in the workplace. Therefore, when MAK values are observed and the substance is classified as pregnancy risk group C, there is no reason to fear damage to the embryo or fetus. N'-(3-aminopropyl)-N'-dodecylpropane-1,3-diamine is not genotoxic or carcinogenic. Due to its corrosive properties, the potential for human contact sensitization cannot be clearly assessed. The substance is not a contact sensitizer for guinea pigs. Skin contact is not expected to significantly cause systemic toxicity.
When rats were given doses of 20 mg/kg body weight and above in the diet for 13 weeks, effects on the kidneys were observed, such as degeneration and necrosis of the tubular epithelium, dilation of the tubules with flattened epithelium and increased tubular basophils. In addition, there were enlarged mesenteric lymph nodes and foamy macrophages. At dose levels of 8 mg/kg body weight and day and above, the species was exposed to the substance in the diet for 52 weeks, and the incidence of lymphohistiocytic myocarditis and lymphohistiocytic infiltration in the skeletal muscle of males and alveolar histiocytosis in the lungs of females was also increased. After 104 weeks of administration of the diet, a dose-dependent increase in the incidence and severity of cardiomyocyte degeneration and skeletal muscle lymphohistiocytic infiltration was observed in male rats at doses of 4 mg/kg bw per day and more than 4 mg/day. In female dogs, after 13 weeks of administration in the diet, the activities of aspartase and alanine aminotransferase in plasma increased at 20 mg/kg bw per day and more than 4 mg/day.

Analysis of N-(3-aminopropyl)-N-dodecylpropane-1,3-diamine in dairy products

Slimani, Kahina, et al. Food chemistry 262 (2018): 168-177.

A novel and robust method for the quantification of N-(3-aminopropyl)-N-dodecylpropane-1,3-diamine residue levels in dairy products using ion-pair reversed-phase liquid chromatography-tandem mass spectrometry (LC-MS/MS) has been developed and fully validated. Sample extraction was performed by salting-out technique using acetonitrile and sodium chloride. For LC-MS/MS, positive electrospray ionization (ESI+) was used to detect the analytes and two multiple reaction monitoring (MRM) transitions were monitored. The method was validated in the range of 5-150 μg kg using the total error method. Therefore, the performance criteria of the method were evaluated. The relative standard deviations for trueness and precision were below 10%; 5 µg kg was excluded for hard pressed cheese for precision. The limits of quantification (LOQ) were approximately 5-7 µg kg, depending on the matrix of interest. The method was successfully used to accurately quantify N-(3-aminopropyl)-N-dodecylpropane-1,3-diamine in 146 dairy products with a maximum contamination level of 225 μg cheese.
Stock solutions of N-(3-aminopropyl)-N-dodecylpropane-1,3-diamine (97%) (referred to as "TA") and isotopically labeled internal standard (> 98%) (referred to as "TA-d") were prepared in HPLC-grade acetonitrile at a concentration of 1 g Lin. Intermediate and working standard solutions were obtained by serial dilution of the standard stock solutions using a mixture of acetonitrile/water (50:50; v/v) and 1% formic acid (v/v). For the internal standard, 1 mg L dilution solutions were prepared from the stock solutions in the same solvent mixture and added before extraction. All prepared solutions were stored at 4°C. The stability of the standard stock solutions was determined to be satisfactory for at least one year. Chromatographic separation was performed using an ultra-high pressure liquid chromatography (UHPLC) system equipped with an autosampler regulated to +10 °C and a column oven maintained at +25 °C. TA was separated at 0 flow rate for 4 mL. The sample extract (10 μL) was injected into the column and the TA was eluted using a binary gradient for 6 min. The mobile phase consisted of water (A) and acetonitrile (B), both containing 25 mM HFBA and 1% formic acid (v/v). The gradient conditions were as follows: linear gradient from 20% to 80% of eluent B from 0 to 3 min; followed by a rapid linear ramp to 20% of eluent B in 0.5 min; a hold of 2.5 min to re-equilibrate the system before the next injection.

Analytical Characterization and Quantification of N-(3-Aminopropyl)-N-dodecylpropane-1,3-diamine Fungicide

Mondin, Andrea, et al. Chemosphere 95 (2014): 379-386.

The triamine N-(3-aminopropyl)-N-dodecylpropane-1,3-diamine (TA) was determined in a raw material called LONZABAC, which is used to formulate a wide range of widely used commercial fungicides. The active ingredient TA is present in LONZABAC at low concentrations along with other molecules. The problem of low purity of the active ingredient was overcome by three independent analytical methods: solution NMR spectroscopy, liquid chromatography coupled to high resolution mass spectrometry (LC/HRMS), and mixed solvent acid-base titration. NMR analysis of the raw material using appropriate internal standards demonstrated the presence of the active ingredients, N-dodecylpropane-1,3-diamine (DA) and n-dodecylamine (MA), in all analyzed batches and the absence of non-organic, NMR inert materials. The results obtained were used to establish a simple, rapid and inexpensive acid-base titration method capable of sufficiently accurate assessment of active ingredients in raw materials and diluted commercial products. For the raw materials, the results were: TA + MA = 91.1 ± 0.8% and DA MA = 8.9 ± 0.8%, in agreement with the LC/MS statistical results. The LC/MS method also demonstrated its great potential for identifying trace biocide ingredients in environmental samples and formulated commercial products.
NMR Analysis 1 H and C NMR spectra were obtained in DMSO-d solutions on a spectrometer operating at 600.01 and 150.07 MHz, respectively. Chemical shift values for H and C are given in d units and referenced to MeSi. The assignments are according to the reported labeling relative to N-(3-Aminopropyl)-N-dodecylpropane-1,3-diamine with the formula CHN. Appropriate integration values for the proton spectra were obtained with a 60-s prescan delay to ensure complete relaxation of all resonances.

N-(3-aminopropyl)-N-dodecylpropane-1,3-diamine for disinfection and protection of historic wooden surfaces

Koziróg, Anna, et al. International Journal of Molecular Sciences 17.8 (2016): 1364.

Effective and safe biocides were selected for disinfection and protection of historic wooden surfaces. Seven active compounds were tested against bacteria and molds, among which didecyldimethylammonium chloride and N-(3-aminopropyl)-N-dodecylpropane-1,3-diamine were effective even at concentrations of 0.02%-2%. Subsequently, eight biocides containing the selected active ingredients were selected and applied three times on the surfaces of wood samples colonized with bacteria and molds. Under laboratory conditions, ABM-1, Boramon and Rocima 101 ensured antimicrobial protection of new wood samples for up to six months. In situ spraying of 30% Boramon and 8% Rocima 101 effectively protected historic wood against bacterial and mold growth for 12 and 3 months, respectively. The color and brightness of new wood did not change after exposure to the biocides. Boramon and Rocima 101 applied by spraying method did not cause significant changes in the color of historic wood. The results of this study were used to develop a procedure for protecting wood in historic buildings from biodegradation.
Microbial susceptibility to active compounds was determined by disc diffusion assay. The surfaces of TSA and MEA were inoculated with bacterial and fungal monocultures (10 CFU/mL and 10 conidia/mL), respectively, and then evenly spread on the surface of the medium. Sterile paper discs (ø 6 mm, Oxoid) were soaked in 15 mL of compound solution at the test concentration; subsequently, the discs were placed on the surface of the medium. The plates were incubated at 30°C for 24-48 h (bacteria) and at 28°C for 48 h (molds). Macroscopic observation of microbial growth was performed, and the diameter of the inhibition zone was calculated. Antimicrobial activity of fungicides was determined by disc diffusion assay. Eight commercial fungicides were used in the study, including N-(3-aminopropyl)-N-dodecylpropane-1,3-diamine.